After a traumatic first encounter with a pizza delivery man, a man struggles with unexpected same-sex desires while trying to return to dating women, only to cross paths with his hookup again at a club.
#transvestite
103 stories tagged with this.
A 15-year-old boy, mocked at school for his feminine appearance, is left home alone when she visits her aunt, and begins exploring his transvestite side.
A married man struggles to resist returning to his 'Suzy' persona after a transformative weekend, as his wife eagerly encourages his feminization.
Kalynn confides to her mother about losing her virgin anal experience with the older Mr. Walker, and her mother reveals she uses sexual favors to advance her career.
A young boy who secretly wears women's clothing discovers transvestite websites and fantasizes about becoming a girl, leading to exploration with a male friend.
A wealthy, self-described "wimp" husband worships his statuesque beauty-queen wife who dominates him in a Mommy/little-boy dynamic with foot fetish and implied cuckolding.
A 17-year-old boyfriend agrees to dress as a cheerleader for his girlfriend's Halloween dorm party, leading to shaved legs, silicone breasts, and an unforgettable night.
A self-described flat-chested man dons sexy lingerie and heads to an adult bookstore across from his hotel, fantasizing about being seen in his forbidden undergarments.
A trans protagonist picks up a heartbroken crossdresser at a club after his partner storms out, exploring attraction across gender presentations.
A young man's vacation takes a transformative turn after losing his clothes, forcing him into an identity change orchestrated by his aunt and sister.
Trump eagerly awaits Manning at his cabin for a wild and filthy encounter, anticipating a night of uninhibited debauchery.
A Trump-themed fan fiction saga continues with a cricket-playing woman reminiscing about her ex-boyfriend before an encounter with the most powerful man in the world.
A satirical political erotic fiction where Trump obsesses over his secret lover while discussing campaign conquests with his jealous chief of staff.
A well-built Irish ex-pat wakes up next to his gorgeous Asian girlfriend and initiates a playful morning seduction that quickly turns dominant.
A mother raises her only son alone and exerts authoritarian control over him, establishing a dynamic built on humiliation.
A feminine man fully transforms into Ruby for a first night out, heading to a bar to explore life as a woman and sex worker.
A submissive man responds to a dominant stranger's AOL chatroom summons and arrives at a dimly lit hotel room to be used and feminized.
A teenage girl dresses her reluctant little brother up like a doll after her parents refuse to buy her the suggestive toy she wants.
A man reconnects with his first love from junior high, who introduces him to a world of feminization and sissification under her dominant guidance.
A man with naturally large breasts recounts how his curious step-daughter repeatedly confronted him about his chest throughout her childhood and into adulthood.